Selective Liquid Phase Hydrogenation of Benzaldehyde to Benzyl Alcohol Over Alumina Supported Gold

Yufen Hao; Chiara Pischetola; Fernando Cardenas-Lizana; Mark A. Keane

doi:10.1007/s10562-019-02944-y

Selective Liquid Phase Hydrogenation of Benzaldehyde to Benzyl Alcohol Over Alumina Supported Gold

Yufen Hao, Chiara Pischetola, Fernando Cardenas-Lizana, Mark A. Keane

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Abstract

We report for the first time 100% benzyl alcohol yield from the liquid phase (T = 353 K, P = 9 bar) hydrogenation of benzaldehyde over Au/Al₂O₃. Under the same reaction conditions, a benchmark Pt/Al₂O₃ catalyst promoted the formation of toluene and benzene as hydrogenolysis by-products. Reaction kinetics was subjected to a Hammett treatment and the reaction constant (ρ = 0.9) was found to be consistent with a nucleophilic mechanism. A solvent (alcohol, water and alcohol + water) effect is demonstrated and ascribed to competitive adsorption where solvation by polar (water) facilitates benzaldehyde activation.

Original language	English
Pages (from-to)	881–887
Number of pages	7
Journal	Catalysis Letters
Volume	150
Early online date	30 Sept 2019
DOIs	https://doi.org/10.1007/s10562-019-02944-y
Publication status	Published - Mar 2020

Keywords

Au/Al O
Benzaldehyde
Benzyl alcohol
Pt/Al O
Selective hydrogenation
Water as solvent

ASJC Scopus subject areas

Catalysis
General Chemistry

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title = "Selective Liquid Phase Hydrogenation of Benzaldehyde to Benzyl Alcohol Over Alumina Supported Gold",

abstract = "We report for the first time 100% benzyl alcohol yield from the liquid phase (T = 353 K, P = 9 bar) hydrogenation of benzaldehyde over Au/Al2O3. Under the same reaction conditions, a benchmark Pt/Al2O3 catalyst promoted the formation of toluene and benzene as hydrogenolysis by-products. Reaction kinetics was subjected to a Hammett treatment and the reaction constant (ρ = 0.9) was found to be consistent with a nucleophilic mechanism. A solvent (alcohol, water and alcohol + water) effect is demonstrated and ascribed to competitive adsorption where solvation by polar (water) facilitates benzaldehyde activation.",

keywords = "Au/Al O, Benzaldehyde, Benzyl alcohol, Pt/Al O, Selective hydrogenation, Water as solvent",

author = "Yufen Hao and Chiara Pischetola and Fernando Cardenas-Lizana and Keane, {Mark A.}",

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pages = "881–887",

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AU - Hao, Yufen

AU - Pischetola, Chiara

AU - Cardenas-Lizana, Fernando

AU - Keane, Mark A.

PY - 2020/3

Y1 - 2020/3

N2 - We report for the first time 100% benzyl alcohol yield from the liquid phase (T = 353 K, P = 9 bar) hydrogenation of benzaldehyde over Au/Al2O3. Under the same reaction conditions, a benchmark Pt/Al2O3 catalyst promoted the formation of toluene and benzene as hydrogenolysis by-products. Reaction kinetics was subjected to a Hammett treatment and the reaction constant (ρ = 0.9) was found to be consistent with a nucleophilic mechanism. A solvent (alcohol, water and alcohol + water) effect is demonstrated and ascribed to competitive adsorption where solvation by polar (water) facilitates benzaldehyde activation.

AB - We report for the first time 100% benzyl alcohol yield from the liquid phase (T = 353 K, P = 9 bar) hydrogenation of benzaldehyde over Au/Al2O3. Under the same reaction conditions, a benchmark Pt/Al2O3 catalyst promoted the formation of toluene and benzene as hydrogenolysis by-products. Reaction kinetics was subjected to a Hammett treatment and the reaction constant (ρ = 0.9) was found to be consistent with a nucleophilic mechanism. A solvent (alcohol, water and alcohol + water) effect is demonstrated and ascribed to competitive adsorption where solvation by polar (water) facilitates benzaldehyde activation.

KW - Au/Al O

KW - Benzaldehyde

KW - Benzyl alcohol

KW - Pt/Al O

KW - Selective hydrogenation

KW - Water as solvent

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U2 - 10.1007/s10562-019-02944-y

DO - 10.1007/s10562-019-02944-y

M3 - Article

SN - 1011-372X

VL - 150

SP - 881

EP - 887

JO - Catalysis Letters

JF - Catalysis Letters

ER -

Selective Liquid Phase Hydrogenation of Benzaldehyde to Benzyl Alcohol Over Alumina Supported Gold

Abstract

Keywords

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